Winter Vacations from $662

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The Latest Winter vacation packages

Price found within the past 48 hours. Click for updated prices.
Indianhead Ironwood Motel

Indianhead Ironwood Motel

2.5 out of 5
Price was $714, price is now $662 per person
$662
per person
Dec 5 - Dec 8
found 7 hours ago
Roundtrip non-stop flight included
Norfolk (ORF) to Ironwood (IWD)
7.8/10 Good! (258 reviews)
the traffic was noisy

Reviewed on Oct 10, 2025

Davos Chalet

Davos Chalet

2 out of 5
Price was $846, price is now $726 per person
$726
per person
Dec 5 - Dec 8
found 7 hours ago
Roundtrip non-stop flight included
Norfolk (ORF) to Ironwood (IWD)
9/10 Wonderful! (67 reviews)
Beautiful property and location!

Reviewed on Oct 12, 2025

Lakeside Haus in Presque Isle

Lakeside Haus in Presque Isle

2 out of 5
Price was $1,187, price is now $1,059 per person
$1,059
per person
Dec 5 - Dec 8
found 7 hours ago
Roundtrip non-stop flight included
Norfolk (ORF) to Ironwood (IWD)
No reviews
Days Inn by Wyndham Hurley

Days Inn by Wyndham Hurley

2 out of 5
Price was $816, price is now $742 per person
$742
per person
Dec 5 - Dec 8
found 7 hours ago
Roundtrip non-stop flight included
Norfolk (ORF) to Ironwood (IWD)
8.4/10 Very Good! (868 reviews)
Great location and a nice stop for our fall color viewing trip

Reviewed on Oct 6, 2025

North Star Retreat-kayak I Swim I Snowmobile

North Star Retreat-kayak I Swim I Snowmobile

2 out of 5
Price was $1,170, price is now $1,081 per person
$1,081
per person
Dec 5 - Dec 8
found 7 hours ago
Roundtrip non-stop flight included
Norfolk (ORF) to Ironwood (IWD)
No reviews
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Winter Hotel Deals

Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin

Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin

Winter
8.2/10 Very Good! (27 reviews)
"The cabin was rustic and homey. The cabin, when closed up all day, had a slight musty smell which cleared easily when the windows open. Overall good for our needs."

Reviewed on Sep 16, 2025

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Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin
5 bedroom 3- bath 8 people capacity pontoon included in Winter Wis.

5 bedroom 3- bath 8 people capacity pontoon included in Winter Wis.

Winter
9.8/10 Exceptional! (65 reviews)
"This house is absolutely amazing! Beautiful inside and out. We loved the pool table and shuffleboard in the garage! We also played card games, went fishing on the great pontoon, watched a movie and sports! It rained a bit but there were beautiful rainbows! This was our second stay and definitely ..."

Reviewed on Sep 21, 2025

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5 bedroom 3- bath 8 people capacity pontoon included in Winter Wis.
Amazing Sunsets, Peaceful, Well Maintained Lake home on Beautiful, Barker lake

Amazing Sunsets, Peaceful, Well Maintained Lake home on Beautiful, Barker lake

Winter
9.6/10 Exceptional! (57 reviews)
"It was fantastic and the owner was awesome. Everything as described. We had a lot of fun."

Reviewed on Sep 1, 2025

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Amazing Sunsets, Peaceful, Well Maintained Lake home on Beautiful, Barker lake
See all 658 properties in Winter
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Winter Essential Information

Language
English
Currency
U.S dollars
Population
310

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Frequently asked questions

How much does a Winter vacation package cost?
You can pick up a vacation package to this popular destination from $662 on Expedia. But how much your vacation to Winter costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Winter?
February, September and November are the best times to search for cheap Winter vacation packages. Traveling in less busy months means you'll typically find reduced prices on hotels and flights.
How many days is enough for Winter?
With a well-planned itinerary, you can easily hit the main Winter sights in a few days. But if you prefer to discover lesser-known spots or take day trips, think about booking your Winter vacation for longer.
How to find the best Winter package deals?
Bagging a cheap Winter package deal is a breeze with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your budget range, add a few filters and see what's available. You can personalize your search by "Amenities," "Property type," "Traveler experience" and more. Sort the results by "Price: low to high" to view the most economical Winter package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Winter vacation as a package?
You can enjoy significant savings on your Winter escape by booking a customized vacation package. Check the "Package" heading, then enter your travel dates and destination to see the best hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Winter?
If you've got your Winter travel dates locked in, book early to score some terrific deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spontaneous adventures? Our last-minute deals are great for setting off on a whim.
Does Expedia offer Book Now, Pay Later Winter vacation packages?
Jet off on your dream trip to Winter with help from our Book Now, Pay Later vacations. No need to scrimp and save or wait for your next paycheck — we've partnered with online lender Affirm to give you flexibility with your finances. Our vacation packages with payment plans allow you to split the cost across 3, 6 or 12 months. With no hidden charges or late payment fees, it's a breeze to budget for your trip and snap up bargains before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.